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Chemical Compound Review:

SureCN132874 (8R,9S,10S,13S,14S)-10,13- dimethyl-9,11,12...

Synonyms: AG-G-34839, CHEMBL2311178, KST-1B6849, AC1L2XNT, LS-19416, ...

Knecht, M. et al., Slama, A. et al., Covey, D.F. et al., Tomaszycki, M.L. et al., Ellinwood, W.E. et al., et al.

Haensel, Slob, Tomaszycki, Banerjee, Adkins-Regan,

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High impact information on 1,4,6-Androstatriene-3,17-dione

Our recent studies with 4-OHA, 4-acetoxyandrostene-3,17-dione, and 1,4,6-androstatriene-3,17-dione indicate that they interact with aromatase by a two-component mechanism, a rapid competitive inhibition, and a slower enzyme inactivation [1].
Recently, it was discovered that 4-hydroxy-4-androstene-3,17-dione, 4-androstene-3,6,17-trione, and 1,4,6-androstatriene-3,17-dione, compounds previously reported to be competitive inhibitors of aromatase, cause a time-dependent loss of aromatase activity in human placental microsomes [2].
Treatment of male monkeys (n = 7) with sc Silastic packets containing the aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD) resulted in 1.5- to 3-fold elevations in serum LH and testosterone concentrations in six of seven animals [3].
When present throughout the 48-h culture period, 4-hydroxy-4-androstene-3,17-dione (4-OHA; greater than or equal to 100 microM) and 1,4,6-androstatriene-3,17-dione (greater than or equal to 5 microM) inhibited FSH-induced LH receptor formation by 40% and 90%, respectively [4].
The necessity of brain aromatization for sexual differentiation was investigated by treating pregnant guinea pigs with an aromatase inhibitor, 1,4,6-androstatriene-3,17-dione (ATD), from Day 30 to Day 55 of gestation [5].

Biological context of 1,4,6-Androstatriene-3,17-dione

Timed-pregnant female rats received daily injections of the aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD; 5 mg/0.2 ml) from the 14th day of pregnancy until parturition [6].
1,4,6-Androstatriene-3,17-dione (ATD), previously reported by us to be an aromatase (estrogen synthetase) inhibitor, was found effective in inhibiting mating and ovulation in the rat [7].
To study the role of endogenous estrogens in functional regression of the monkey corpus luteum, we administered the aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD) to rhesus monkeys during the luteal phase of the menstrual cycle [8].
Two groups of rats were used: normal males and males with impaired masculine sexual behavior due to neonatal treatment with the aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD) [9].
These results indicate that the length of the n-alkyl substituent at C-6 of androsta-1,4,6-triene-3,17-dione (6h), rather than its 4,6-diene analog 5h, plays a critical role in tight binding to the active site of aromatase [10].

Anatomical context of 1,4,6-Androstatriene-3,17-dione

Administration of the aromatase inhibitor, androsta-1,4,6-triene-3,17-dione (ATD) on Days 5-8 of pregnancy prevented implantation of blastocysts on Day 13 [11].
The hypothalamus in situ efficiently converted [3H]androstenedione to [3H]estrone and this aromatization was inhibited by the presence of androsta-1,4,6-triene-3,17-dione (ATD) in the perfusate [12].
The in-vitro effects of oestradiol and testosterone, alone or together with an aromatase inhibitor (1,4,6-androstatriene-3,17-dione), on the appearance of progesterone receptor (PR) in the pituitary were studied in the chick embryo [13].
The compound was tested in vitro in primary dissociated cell cultures made from hatching telencephalon and compared to a commonly used inhibitor, 1,4,6-androstatriene-3,17-dione (ATD) [14].

Associations of 1,4,6-Androstatriene-3,17-dione with other chemical compounds

Both aromatase inhibitors caused relatively greater inhibition of LH receptor formation when added from 20-48 h of culture, the period during which FSH-stimulated estrogen synthesis occurs (85% maximal inhibition with 4-OHA and 95% with 1,4,6-androstatriene-3,17-dione) [4].
Effect of an inhibitor of aromatization, 1,4,6 androstatriene-3,17-dione (ATD) on LH release and steroid binding in hypothalamus of adult female rats [15].
We examined the effects of an aromatase inhibitor, 1,4,6-androstatriene-3,17-dione (ATD), combined with an anti-androgen, flutamide (F), on the behavior and pairing status of initially unpaired male and female zebra finches (Taeniopygia guttata) [16].

Gene context of 1,4,6-Androstatriene-3,17-dione

Exogenous aromatase inhibitors (1,4,6-androstatriene-3,17-dione or fadrozole) suppressed aromatase activity in the brain [17].
Effects of age and 1,4,6-androstatriene-3,17-dione on activities of hCG-induced 19-hydroxylase and aromatase of rat testes [18].

Analytical, diagnostic and therapeutic context of 1,4,6-Androstatriene-3,17-dione

Prevention of testosterone aromatization in the female rat pups by perinatal treatment with 1,4,6 androstatriene-3,17-dione (ATD) induces an important defeminization as shown by a reduction of fluctuations of LH release after castration and estradiol implantation [15].
MN-POA/AH formation was inhibited in males deprived prenatally of estrogenic stimulation via maternal ovariectomy and subcutaneous implantation of the aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD) on gestational day 30 [19].
Immunological interference of the synthetic aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD) and its metabolite(s) in the radioimmunoassay for testosterone [20].

References

Effects of aromatase inhibitor 4-hydroxyandrostenedione and other compounds in the 7, 12-dimethylbenz(a)anthracene-induced breast carcinoma model. Brodie, A.M., Garrett, W.M., Hendrickson, J.R., Tsai-Morris, C.H. Cancer Res. (1982) [Pubmed]
A new hypothesis based on suicide substrate inhibitor studies for the mechanism of action of aromatase. Covey, D.F., Hood, W.F. Cancer Res. (1982) [Pubmed]
Inhibition of aromatization stimulates luteinizing hormone and testosterone secretion in adult male rhesus monkeys. Ellinwood, W.E., Hess, D.L., Roselli, C.E., Spies, H.G., Resko, J.A. J. Clin. Endocrinol. Metab. (1984) [Pubmed]
Aromatase inhibitors prevent granulosa cell differentiation: an obligatory role for estrogens in luteinizing hormone receptor expression. Knecht, M., Brodie, A.M., Catt, K.J. Endocrinology (1985) [Pubmed]
Prenatal inhibition of aromatase activity affects luteinizing hormone feedback mechanisms and reproductive behaviors of adult guinea pigs. Choate, J.V., Resko, J.A. Biol. Reprod. (1994) [Pubmed]
Organizational effects of testosterone via aromatization on feminine reproductive behavior and neural progestin receptors in rat brain. Parsons, B., Rainbow, T.C., McEwen, B.S. Endocrinology (1984) [Pubmed]
Antifertility effects of an aromatase inhibitor, 1,4,6-androstatriene-3, 17-dione. Brodie, A.M., Wu, J.T., Marsh, D.A., Brodie, H.J. Endocrinology (1979) [Pubmed]
Effect of inhibition of estrogen synthesis during the luteal phase on function of the corpus luteum in rhesus monkeys. Ellinwood, W.E., Resko, J.A. Biol. Reprod. (1983) [Pubmed]
Flesinoxan: a prosexual drug for male rats. Haensel, S.M., Slob, A.K. Eur. J. Pharmacol. (1997) [Pubmed]
6-Alkylandrosta-4,6-diene-3,17-diones and their 1,4,6-triene analogs as aromatase inhibitors. Structure-activity relationships. Numazawa, M., Oshibe, M., Yamaguchi, S. Steroids (1997) [Pubmed]
Is estrogen required for implantation in the ferret? Mead, R.A., McRae, M. Biol. Reprod. (1982) [Pubmed]
In situ subcellular distribution and metabolism of progesterone, estradiol and androstenedione in the vascularly separated and isolated hypothalamus of the female rhesus monkey. Billiar, R.B., Takaoka, Y., Johnson, W., White, R.J., Little, B. Neuroendocrinology (1981) [Pubmed]
Evidence of a functional aromatase system in the pituitary gland of the chick embryo in vitro. Guennoun, R., Gasc, J.M. J. Endocrinol. (1988) [Pubmed]
Fadrozole: a potent and specific inhibitor of aromatase in the zebra finch brain. Wade, J., Schlinger, B.A., Hodges, L., Arnold, A.P. Gen. Comp. Endocrinol. (1994) [Pubmed]
Effect of an inhibitor of aromatization, 1,4,6 androstatriene-3,17-dione (ATD) on LH release and steroid binding in hypothalamus of adult female rats. Slama, A., Gogan, F., Sarrieau, A., Vial, M., Rostene, W., Kordon, C. Experimental brain research. Experimentelle Hirnforschung. Expérimentation cérébrale. (1986) [Pubmed]
The role of sex steroids in courtship, pairing and pairing behaviors in the socially monogamous zebra finch. Tomaszycki, M.L., Banerjee, S.B., Adkins-Regan, E. Hormones and behavior. (2006) [Pubmed]
Sex change in the protandrous black porgy, Acanthopagrus schlegeli: a review in gonadal development, estradiol, estrogen receptor, aromatase activity and gonadotropin. Lee, Y.H., Du, J.L., Yueh, W.S., Lin, B.Y., Huang, J.D., Lee, C.Y., Lee, M.F., Lau, E.L., Lee, F.Y., Morrey, C., Nagahama, Y., Chang, C.F. J. Exp. Zool. (2001) [Pubmed]
Effects of age and 1,4,6-androstatriene-3,17-dione on activities of hCG-induced 19-hydroxylase and aromatase of rat testes. Inano, H., Lin, Y.C., Dym, M. J. Steroid Biochem. (1982) [Pubmed]
Differentiation in male ferrets of a sexually dimorphic nucleus of the preoptic/anterior hypothalamic area requires prenatal estrogen. Tobet, S.A., Zahniser, D.J., Baum, M.J. Neuroendocrinology (1986) [Pubmed]
Immunological interference of the synthetic aromatase inhibitor 1,4,6-androstatriene-3,17-dione (ATD) and its metabolite(s) in the radioimmunoassay for testosterone. Donaldson, M.D., Forest, M.G. Steroids (1980) [Pubmed]

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